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Glycerol group-containing organopolysiloxane, cosmetic, and method for producing glycerol group-containing organopolysiloxane

a technology of organopolysiloxane and glycerol group, which is applied in the field of cosmetics, and methods for producing glycerol group containing organopolysiloxane, can solve the problems of unavoidable breakage or rearrangement of siloxane chain by presence of acid or base catalyst, and achieve good durability of moist feeling

Active Publication Date: 2013-11-12
SHIN ETSU CHEM IND CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

The patent text describes a cosmetic that does not have an odor over time and gives a good moist feel without being too sticky or grating. This is achieved by using a specific type of organopolysiloxane with glycerol groups. This new type of organopolysiloxane can be easily obtained without special purification processes and is used in the cosmetic without causing any issues.

Problems solved by technology

However, in this method, a starting glycerol having a double bond at its terminal (unreacted glycerol) remains inevitably, so that purification processes such as washing and a hydrogenation reaction are absolutely imperative.
It is known that, if these purification processes are not carried out, unpleasant odor is generated with passage of time.
Alternatively, a reaction method wherein a hydroxy-containing silicone is reacted with a glycidol in the presence of an acid or a base catalyst is known; but in this method, there is such a problem that breakage or rearrangement of a siloxane chain by presence of an acid or a base catalyst is unavoidable.
However, although a conventional glycerol group-containing organopolysiloxane, if blended in a cosmetic, can give a moist feeling because of its excellent water holding ability, there have been problems of stickiness and poor durability of the moist feeling.

Method used

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  • Glycerol group-containing organopolysiloxane, cosmetic, and method for producing glycerol group-containing organopolysiloxane
  • Glycerol group-containing organopolysiloxane, cosmetic, and method for producing glycerol group-containing organopolysiloxane
  • Glycerol group-containing organopolysiloxane, cosmetic, and method for producing glycerol group-containing organopolysiloxane

Examples

Experimental program
Comparison scheme
Effect test

preparation example 1

[0104]Into a reactor were taken 300 parts by mass of an amino-modified organopolysiloxane shown by the following average composition formula with viscosity of 38 mm2 / second (25° C.) and amine equivalent of 2500 g / mol,

[0105]

50 parts by mass of tetrahydrofuran, and 12 parts by mass of succinic anhydride; and then, the resulting mixture was stirred at 50° C. for 3 hours. The reaction mixture thus obtained was stripped to remove the solvent under reduced pressure at 110° C. to obtain a colorless, transparent liquid having viscosity of 550 mm2 / second (25° C.). The carboxy equivalent of this liquid was 2630 g / mol, so that it was confirmed that conversion to the amidecarboxylic acid took place.

[0106]Then, 150 parts by mass of the liquid thus obtained and 6 parts by mass of glycidol were stirred in a different reactor at 110° C. for 8 hours. The reaction mixture thus obtained was stripped to remove the unreacted substance under reduced pressure at 120° C. to obtain a pale yellow, transparen...

preparation example 2

[0108]Into a reactor were taken 200 parts by mass of an amino-modified organopolysiloxane shown by the following average composition formula with viscosity of 57 mm2 / second (25° C.) and amine equivalent of 1230 g / mol,

[0109]

20 parts by mass of tetrahydrofuran, and 16 parts by mass of succinic anhydride; and then, the resulting mixture was stirred at 50° C. for 3 hours. The reaction mixture thus obtained was stripped to remove the solvent under reduced pressure at 110° C. to obtain a colorless, transparent liquid having viscosity of 7600 mPa·s (25° C.). The carboxy equivalent of this liquid was 1340 g / mol, so that it was confirmed that conversion to the amidecarboxylic acid took place.

[0110]Then, 120 parts by mass of the liquid thus obtained, 13 parts by mass of glycidol, and 30 parts by mass of acetonitrile were stirred in a different reactor at 65° C. for 6 hours. The reaction mixture thus obtained was stripped to remove the solvent and the unreacted substance under reduced pressure...

preparation example 3

[0112]Into a reactor were taken 150 parts by mass of an amino-modified organopolysiloxane shown by the following average composition formula with viscosity of 110 mm2 / second (25° C.) and amine equivalent of 5090 g / mol,

[0113]

20 parts by mass of tetrahydrofuran, and 3 parts by mass of succinic anhydride; and then, the resulting mixture was stirred at 50° C. for 3 hours. The reaction mixture thus obtained was stripped to remove the solvent under reduced pressure at 110° C. to obtain a colorless, transparent liquid having viscosity of 1260 mPa·s (25° C.). The carboxy equivalent of this liquid was 5240 g / mol, so that it was confirmed that conversion to the amidecarboxylic acid took place.

[0114]Then, 120 parts by mass of the liquid thus obtained, 9 parts by mass of glycidol, 0.2 parts by mass of triethylamine, and 30 parts by mass of tetrahydrofurane were stirred in a different reactor at 80° C. for 6 hours. The reaction mixture thus obtained was stripped to remove the solvent and the unr...

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Abstract

There is disclosed a novel glycerol group-containing organopolysiloxane is formed of a glycerol group-containing substituent shown by the following general formula (1) which is bonded to at least one silicon atom of a main chain organopolysiloxane segment,wherein each X and Y independently represents a divalent hydrocarbon group having 1 to 10 carbon atoms; m represents an integer of 0 to 4; and Z represents an organic group shown by the following general formula (2),wherein Ra represents a divalent hydrocarbon group having 2 to 12 carbon atoms; and m′ represents an integer of 1 to 5. As a result, there is provided a novel glycerol group-containing organopolysiloxane and a method for producing it without requiring special purification processes, and in addition, provided is a cosmetic not generating an odor with passage of time while giving a moist feeling without stickiness.

Description

BACKGROUND OF THE INVENTION[0001]1. Field of the Invention[0002]The present invention relates to a novel glycerol group-containing organopolysiloxane, a cosmetic containing this, and a method for producing a glycerol group-containing organopolysiloxane.[0003]2. Description of the Related Art[0004]So far, methods for connecting a glycerol group to a silicone (Patent Documents 1 to 4) and compounds obtained by these methods have been disclosed. In these methods, an intended glycerol group-containing organopolysiloxane was obtained by a catalytic addition reaction of a glycerol having a double bond at its terminal ((poly)glycerin having an aliphatic unsaturated bond) or a derivative thereof with a methyl hydrogen polysiloxane.[0005]However, in this method, a starting glycerol having a double bond at its terminal (unreacted glycerol) remains inevitably, so that purification processes such as washing and a hydrogenation reaction are absolutely imperative. It is known that, if these purif...

Claims

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Application Information

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Patent Type & Authority Patents(United States)
IPC IPC(8): A61K31/74
CPCC08G77/388A61Q5/12A61Q19/00A61K8/898A61Q1/02A61Q3/00A61Q5/04A61Q5/06A61Q5/08A61Q5/10A61Q17/04A61K2800/10A61K8/89C08G77/16C08G77/46C08L83/06
Inventor MORIYA, HIROYUKI
Owner SHIN ETSU CHEM IND CO LTD